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Chemoselective methionine 18F-fluorination on unprotected peptides for positron-emission tomography imaging

Research Project

Project/Area Number 19K17156
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 52040:Radiological sciences-related
Research InstitutionNational Institutes for Quantum Science and Technology

Principal Investigator

Hu Kuan  国立研究開発法人量子科学技術研究開発機構, 量子医科学研究所 先進核医学基盤研究部, 研究員 (00827678)

Project Period (FY) 2019-04-01 – 2022-03-31
Project Status Discontinued (Fiscal Year 2021)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2021: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2020: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordspeptide / fluorine 18 / radiolabeling / PET / cancer / diagnosis / methionine / 18F-fluorination / chemoselective / ReACT / oxaziridine / radiotracer / Peptide / PET tracer / ozaxiridine / 18F labeling / 18F bioconjugatoin / Methionine / PET imaging
Outline of Research at the Start

A strategy for chemoselective radio-methionine bioconjugation through a redox-activated chemical tagging (ReACT), using oxaziridine-based 18F-reagent to achieve highly selective, rapid, and robust methionine labeling under biocompatible reaction conditions.

Outline of Final Research Achievements

PET imaging is a highly clinically relevant technique for disease diagnosis. A series of PET radiotracers have been approved for clinical use. As one class of PET tracers, peptide-based radiotracers have many advantages due to their favorable pharmacokinetics and biodistribution profiles. The development of peptide-based PET tracers is emerging as one of the most vital task for nuclear medicine, while the direct labeling of unprotected peptides without prothestic group remains a challenge. 18F is an positron emission radionuclide with a decay hald-life of 109.8 min, showing a good matchness with the biological half-life of peptides. In this context, the radiolabeling of peptide with 18F is attracting more and more attention from both industry and acedamia. In this project, we developed a non-prothestic, bioconjugated method for direct 18F labeling of unprotected peptides with methionine residues.The method is generally applicable for radiolabeling any Met-containing peptides.

Academic Significance and Societal Importance of the Research Achievements

This resarch results may help develop imaging agents that can be used for disease diagnosis in hospticals. Our research provide a feasible method to synthesize imaging agents via an more financially econimic way, thus save cost for patients.Moreover, it can reduce radiation to the human body.

Report

(3 results)
  • 2021 Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Research-status Report
  • Research Products

    (34 results)

All 2021 2020 2019

All Journal Article (21 results) (of which Int'l Joint Research: 21 results,  Peer Reviewed: 21 results,  Open Access: 6 results) Presentation (13 results) (of which Int'l Joint Research: 7 results,  Invited: 1 results)

  • [Journal Article] Flexible Supercapacitors Based on Graphene/Boron Nitride Nanosheets Electrodes and PVA/PEI Gel Electrolytes2021

    • Author(s)
      Wang Chan、Hu Kuan、Liu Ying、Zhang Ming-Rong、Wang Zhiwei、Li Zhou
    • Journal Title

      Materials

      Volume: 14 Issue: 8 Pages: 1955-1955

    • DOI

      10.3390/ma14081955

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Recent developments on PET radiotracers for TSPO and their applications in neuroimaging2021

    • Author(s)
      Zhang Lingling、Hu Kuan、Shao Tuo、Hou Lu、Zhang Shaojuan、Ye Weijian、Josephson Lee、Meyer Jeffrey H.、Zhang Ming-Rong、Vasdev Neil、Wang Jinghao、Xu Hao、Wang Lu、Liang Steven H.
    • Journal Title

      Acta Pharmaceutica Sinica B

      Volume: 11 Issue: 2 Pages: 373-393

    • DOI

      10.1016/j.apsb.2020.08.006

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Development of a highly-specific 18F-labeled irreversible positron emission tomography tracer for monoacylglycerol lipase mapping2021

    • Author(s)
      Chen Zhen、Mori Wakana、Rong Jian、Schafroth Michael A.、Shao Tuo、Van Richard S.、Ogasawara Daisuke、Yamasaki Tomoteru、Hiraishi Atsuto、Hatori Akiko、Chen Jiahui、Zhang Yiding、Hu Kuan、Fujinaga Masayuki、Sun Jiyun、Yu Qingzhen、Collier Thomas L.、et al.
    • Journal Title

      Acta Pharmaceutica Sinica B

      Volume: In press Issue: 6 Pages: 1686-1695

    • DOI

      10.1016/j.apsb.2021.01.021

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] PET Imaging of VEGFR with a Novel 64Cu-Labeled Peptide2020

    • Author(s)
      Hu Kuan、Shang Jingjie、Xie Lin、Hanyu Masayuki、Zhang Yiding、Yang Zhimin、Xu Hao、Wang Lu、Zhang Ming-Rong
    • Journal Title

      ACS Omega

      Volume: 5 Issue: 15 Pages: 8508-8514

    • DOI

      10.1021/acsomega.9b03953

    • Related Report
      2020 Annual Research Report 2019 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Harnessing the PD-L1 interface peptide for positron emission tomography imaging of the PD-1 immune checkpoint2020

    • Author(s)
      Hu Kuan、Xie Lin、Hanyu Masayuki、Zhang Yiding、Li Lingyun、Ma Xiaohui、Nagatsu Kotaro、Suzuki Hisashi、Wang Weizhi、Zhang Ming-Rong
    • Journal Title

      RSC Chemical Biology

      Volume: 1 Issue: 4 Pages: 214-224

    • DOI

      10.1039/d0cb00070a

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Marriage of black phosphorus and Cu2+ as effective photothermal agents for PET-guided combination cancer therapy2020

    • Author(s)
      Hu Kuan、Xie Lin、Zhang Yiding、Hanyu Masayuki、Yang Zhimin、Nagatsu Kotaro、Suzuki Hisashi、Ouyang Jiang、Ji Xiaoyuan、Wei Junjie、Xu Hao、Farokhzad Omid C.、Liang Steven H.、Wang Lu、Tao Wei、Zhang Ming-Rong
    • Journal Title

      Nature Communications

      Volume: 11 Issue: 1 Pages: 2778-2778

    • DOI

      10.1038/s41467-020-16513-0

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Self-Assembly of Constrained Cyclic Peptides Controlled by Ring Size2020

    • Author(s)
      Hu Kuan、Xiong Wei、Sun Chengjie、Wang Chan、Li Jingxu、Yin Feng、Jiang Yixiang、Zhang Ming-Rong、Li Zhou、Wang Xinwei、Li Zigang
    • Journal Title

      CCS Chemistry

      Volume: 2 Issue: 1 Pages: 42-51

    • DOI

      10.31635/ccschem.020.201900047

    • Related Report
      2020 Annual Research Report 2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Boron agents for neutron capture therapy2020

    • Author(s)
      Hu Kuan、Yang Zhimin、Zhang Lingling、Xie Lin、Wang Lu、Xu Hao、Josephson Lee、Liang Steven H.、Zhang Ming-Rong
    • Journal Title

      Coordination Chemistry Reviews

      Volume: 405 Pages: 213139-213139

    • DOI

      10.1016/j.ccr.2019.213139

    • Related Report
      2020 Annual Research Report 2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Customization of Conductive Elastomer Based on PVA/PEI for Stretchable Sensors2020

    • Author(s)
      Wang Chan、Hu Kuan、Zhao Chaochao、Zou Yang、Liu Ying、Qu Xuecheng、Jiang Dongjie、Li Zhe、Zhang Ming‐Rong、Li Zhou
    • Journal Title

      Small

      Volume: 16 Issue: 7 Pages: 1904758-1904758

    • DOI

      10.1002/smll.201904758

    • Related Report
      2020 Annual Research Report 2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Smart Titanium Coating Composed of Antibiotic Conjugated Peptides as an Infection‐Responsive Antibacterial Agent2020

    • Author(s)
      Zhang Yunfei、Hu Kuan、Xing Xuan、Zhang Jingshuang、Zhang Ming‐Rong、Ma Xiaohui、Shi Rui、Zhang Liqun
    • Journal Title

      Macromolecular Bioscience

      Volume: 21 Issue: 1 Pages: 2000194-2000194

    • DOI

      10.1002/mabi.202000194

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis and preliminary evaluation of 4-hydroxy-6-(3-[11C]methoxyphenethyl)pyridazin-3(2H)-one, a 11C-labeled -amino acid oxidase (DAAO) inhibitor for PET imaging2020

    • Author(s)
      Deng Xiaoyun、Zhang Yiding、Chen Zhen、Kumata Katsushi、Van Richard、Rong Jian、Shao Tuo、Hatori Akiko、Mori Wakana、Yu Qingzhen、Hu Kuan、Fujinaga Masayuki、Wey Hsiao-Ying、Shao Yihan、Josephson Lee、Murtas Giulia、Pollegioni Loredano、Zhang Ming-Rong、Liang Steven
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters

      Volume: 30 Issue: 16 Pages: 127326-127326

    • DOI

      10.1016/j.bmcl.2020.127326

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis and preliminary evaluation of 18F-labeled 1-(6,7-dimethyl-4-(methylamino)-1,3-dihydro-2H-pyrrolo[3,4-c]pyridin-2-yl)-2-(trans-2-(6-fluoropyridin-3-yl)cyclopropyl)ethan-1-one for imaging muscarinic acetylcholine receptor subtype 42020

    • Author(s)
      Deng Xiaoyun、Zhang Yiding、Rong Jian、Kumata Katsushi、Shao Tuo、Wang Gangqiang、Hatori Akiko、Mori Wakana、Yu Qingzhen、Hu Kuan、Fujinaga Masayuki、Shao Yihan、Josephson Lee、Sun Shaofa、Zhang Ming-Rong、Liang Steven
    • Journal Title

      Tetrahedron Letters

      Volume: 61 Issue: 27 Pages: 152060-152060

    • DOI

      10.1016/j.tetlet.2020.152060

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Radiotheranostic Agent 64Cu-cyclam-RAFT-c(-RGDfK-)4 for Management of Peritoneal Metastasis in Ovarian Cancer2020

    • Author(s)
      Jin Zhao-Hui、Tsuji Atsushi B.、Degardin Melissa、Sugyo Aya、Obara Satoshi、Wakizaka Hidekatsu、Nagatsu Kotaro、Hu Kuan、Zhang Ming-Rong、Dumy Pascal、Boturyn Didier、Higashi Tatsuya
    • Journal Title

      Clinical Cancer Research

      Volume: 26 Issue: 23 Pages: 6230-6241

    • DOI

      10.1158/1078-0432.ccr-20-1205

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] 3-(Cyclopropylmethyl)-7-((4-(4-[11C]methoxyphenyl)piperidin-1-yl)methyl)-8-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine: Synthesis and preliminary evaluation for PET imaging of metabotropic glutamate receptor subtype 22020

    • Author(s)
      Kumata Katsushi、Zhang Yiding、Ogawa Masanao、Kurihara Yusuke、Mori Wakana、Hu Kuan、Fujinaga Masayuki、Nengaki Nobuki、Zhang Ming-Rong
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters

      Volume: 30 Issue: 23 Pages: 127555-127555

    • DOI

      10.1016/j.bmcl.2020.127555

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] A Hybrid Biofuel and Triboelectric Nanogenerator for Bioenergy Harvesting2020

    • Author(s)
      Li Hu、Zhang Xiao、Zhao Luming、Jiang Dongjie、Xu Lingling、Liu Zhuo、Wu Yuxiang、Hu Kuan、Zhang Ming-Rong、Wang Jiangxue、Fan Yubo、Li Zhou
    • Journal Title

      Nano-Micro Letters

      Volume: 12 Issue: 1 Pages: 50-50

    • DOI

      10.1007/s40820-020-0376-8

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Identification and Development of a New Positron Emission Tomography Ligand 4-(2-Fluoro-4-[11C]methoxyphenyl)-5-((1-methyl-1H-pyrazol-3-yl)methoxy)picolinamide for Imaging Metabotropic Glutamate Receptor Subtype 2 (mGlu2)2020

    • Author(s)
      Yamasaki Tomoteru、Zhang Xiaofei、Kumata Katsushi、Zhang Yiding、Deng Xiaoyun、Fujinaga Masayuki、Chen Zhen、Mori Wakana、Hu Kuan、Wakizaka Hidekatsu、Hatori Akiko、Xie Lin、Ogawa Masanao、Nengaki Nobuki、Van Richard、Shao Yihan、Sheffler Douglas J.、Cosford Nicholas D. P.、Liang Steven H.、Zhang Ming-Rong
    • Journal Title

      Journal of Medicinal Chemistry

      Volume: 63 Issue: 20 Pages: 11469-11483

    • DOI

      10.1021/acs.jmedchem.9b01991

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis and evaluation of 6-(11C-methyl(4-(pyridin-2-yl)thiazol-2-yl)amino)benzo[d]thiazol-2(3H)-one for imaging γ-8 dependent transmembrane AMPA receptor regulatory protein by PET2020

    • Author(s)
      Yu Qingzhen、Kumata Katsushi、Li Hua、Zhang Yiding、Chen Zhen、Zhang Xiaofei、Shao Tuo、Hatori Akiko、Yamasaki Tomoteru、Xie Lin、Hu Kuan、Wang Gangqiang、Josephson Lee、Sun Shaofa、Zhang Ming-Rong、Liang Steven H.
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters

      Volume: 30 Issue: 4 Pages: 126879-126879

    • DOI

      10.1016/j.bmcl.2019.126879

    • Related Report
      2020 Annual Research Report 2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis and preliminary studies of 11C-labeled tetrahydro-1,7-naphthyridine-2-carboxamides for PET imaging of metabotropic glutamate receptor 22020

    • Author(s)
      Zhang Xiaofei、Zhang Yiding、Chen Zhen、Shao Tuo、Van Richard、Kumata Katsushi、Deng Xiaoyun、Fu Hualong、Yamasaki Tomoteru、Rong Jian、Hu Kuan、Hatori Akiko、Xie Lin、Yu Qingzhen、Ye Weijian、Xu Hao、Sheffler Douglas J.、Cosford Nicholas D. P.、Shao Yihan、Tang Pingping、Wang Lu、Zhang Ming-Rong、Liang Steven H.
    • Journal Title

      Theranostics

      Volume: 10 Issue: 24 Pages: 11178-11196

    • DOI

      10.7150/thno.42587

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis and preliminary evaluation of novel 11C-labeled GluN2B-selective NMDA receptor negative allosteric modulators2020

    • Author(s)
      Sun Ji-yun、Kumata Katsushi、Chen Zhen、Zhang Yi-ding、Chen Jia-hui、Hatori Akiko、Fu Hua-long、Rong Jian、Deng Xiao-yun、Yamasaki Tomoteru、Xie Lin、Hu Kuan、Fujinaga Masayuki、Yu Qing-zhen、Shao Tuo、Collier Thomas Lee、Josephson Lee、Shao Yi-han、Du Yun-fei、Wang Lu、Xu Hao、Zhang Ming-rong、Liang Steven H
    • Journal Title

      Acta Pharmacologica Sinica

      Volume: 42 Issue: 3 Pages: 491-498

    • DOI

      10.1038/s41401-020-0456-9

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] 131I-IITM and 211At-AITM: Two Novel Small-Molecule Radiopharmaceuticals Targeting Oncoprotein Metabotropic Glutamate Receptor 12019

    • Author(s)
      Xie Lin、Hanyu Masayuki、Fujinaga Masayuki、Zhang Yiding、Hu Kuan、Minegishi Katsuyuki、Jiang Cuiping、Kurosawa Fuki、Morokoshi Yukie、Li Huizi Keiko、Hasegawa Sumitaka、Nagatsu Kotaro、Zhang Ming-Rong
    • Journal Title

      Journal of Nuclear Medicine

      Volume: 61 Issue: 2 Pages: 242-248

    • DOI

      10.2967/jnumed.119.230946

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Radiosynthesis and evaluation of a novel monoacylglycerol lipase radiotracer: 1,1,1,3,3,3-hexafluoropropan-2-yl-3-(1-benzyl-1H-pyrazol-3-yl)azetidine-1-[11C]carboxylate2019

    • Author(s)
      Mori Wakana、Hatori Akiko、Zhang Yiding、Kurihara Yusuke、Yamasaki Tomoteru、Xie Lin、Kumata Katsushi、Hu Kuan、Fujinaga Masayuki、Zhang Ming-Rong
    • Journal Title

      Bioorganic & Medicinal Chemistry

      Volume: 27 Issue: 16 Pages: 3568-3573

    • DOI

      10.1016/j.bmc.2019.06.037

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] RADIOLABELLING AND PET IMAGING OF COPPER-64 LABELED ISODGR DERIVATIVE2021

    • Author(s)
      Masayuki Hanyu , Lin Xie , Hu Kuan , Yiding Zhang , Ming-Rong Zhang
    • Organizer
      第57回ペプチド討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Whole-body PET Tracking of a D-dodecapeptide and its Radiotheranostic Potential for PD-L1 overexpressed tumors2021

    • Author(s)
      Hu Kuan , Xie Lin , Yiding Zhang , Hanyu Masayuki , Zhang Ming-Rong
    • Organizer
      SNMMI2021
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] PET imaging of PD-L1 overexpressing tumors with a 68Ga labeled D-dodecapeptide2021

    • Author(s)
      Hu Kuan , Xie Lin , Hanyu Masayuki , Yiding Zhang , Zhang Ming-Rong
    • Organizer
      eSRS
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] PEGylation modulation of peptides promotes PET detection of cancers2021

    • Author(s)
      Hu Kuan , Xie Lin , Yiding Zhang , Hanyu Masayuki , Zhang Ming-Rong
    • Organizer
      eSRS
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Stapled Peptide-based radiotheranostics agent targeting MDM2 suppresses p53-mutant tumor growth2021

    • Author(s)
      Hu Kuan , Xie Lin , Yiding Zhang , Hanyu Masayuki , Zhang Ming-Rong
    • Organizer
      SNMMI2021 ANNUAL MEETING
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Positron Emission Tomography Imaging of Vascular Endothelial Growth Factor Receptor Expression with a new 64Cu labeled peptide2020

    • Author(s)
      Hu, Kuan Shang, Jingjie Xie, Lin Hanyu, Masayuki Zhang, Yiding Yang, Zhimin Yang, Zhimin Xu, Hao Wang, Lu Zhang, Ming-Rong
    • Organizer
      SNMMI 2020 Annual Meeting
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of novel 18F-labeled PET tracers for imaging TSPO with insensitivity to rs6971 polymorphism2020

    • Author(s)
      Lingling Zhang , Masayuki Fujinaga , Bin Ji , Hu Kuan , Weijian Ye , Lin Xie , Yiding Zhang , Lu Hou , Hao Xu , Ming-Rong Zhang , Wang Lu
    • Organizer
      SNMMI 2020 Annual Meeting
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] PET Imaging of VEGFR with a Novel <SUP>64</SUP>Cu Labeled Peptide2020

    • Author(s)
      Hu Kuan , Lin Xie , Yiding Zhang , Masayuki Hanyu , Ming-Rong Zhang
    • Organizer
      第60回日本核医学会学術総会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Harnessing PD-L1 interface peptide for PET imaging of PD-1 immune checkpoint2020

    • Author(s)
      Hu Kuan , Lin Xie , Yiding Zhang , Masayuki Hanyu , Ming-Rong Zhang
    • Organizer
      第60回日本核医学会学術総会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 癌蛋白質mGluR1に基づくがん種横断的な211At-AITM標的アイソトープ治療法の開発2020

    • Author(s)
      謝 琳 , 張 露露 , 破入 正行 , 藤永 雅之 , 張 一鼎 , 峯岸 克行 , Hu Kuan , 李 惠子 , 長谷川 純崇 , 永津 弘太郎 , 張 明栄
    • Organizer
      第60回日本核医学会学術総会
    • Related Report
      2020 Annual Research Report
  • [Presentation] PET imaging of VEGFR-2 with a novel 64Cu labeled peptide2019

    • Author(s)
      Hu Kuan, Ming-Rong Zhang
    • Organizer
      第19回放射性医薬品・画像診断薬研究会での口頭発表
    • Related Report
      2019 Research-status Report
  • [Presentation] Dual targeting of PD-L1 and integrin for preclinical PET imaging of cancers2019

    • Author(s)
      Hu Kuan
    • Organizer
      第59回日本核医学会学術総会
    • Related Report
      2019 Research-status Report
  • [Presentation] Develop a peptide-based PET radiotracer for imaging PD-L1 expression in cancer2019

    • Author(s)
      Hu Kuan, Lin Xie, Masayuki Hanyu, Yiding Zhang, Ming-Rong Zhang
    • Organizer
      ISRS2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited

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Published: 2019-04-18   Modified: 2023-01-30  

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